Ethanolamine → HCID 49770157, compound

HRID 1157764Notes

Reaction equation

[F:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:12]=[C:11]([C:13](OCC)=[O:14])[N:10]([CH3:18])[N:9]=2)=[C:4]2[NH:19][CH:20]=[C:21]([C:22](=[O:42])[C:23](=[O:41])[N:24]3[CH2:29][CH2:28][N:27]([C:30]4[N:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[N:33]=[N:32][N:31]=4)[CH2:26][CH2:25]3)[C:3]=12.[CH2:43]([CH2:45][NH2:46])[OH:44]>CN(C=O)C>[F:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH:46][CH2:45][CH2:43][OH:44])=[O:14])[N:10]([CH3:18])[N:9]=2)=[C:4]2[NH:19][CH:20]=[C:21]([C:22](=[O:42])[C:23](=[O:41])[N:24]3[CH2:25][CH2:26][N:27]([C:30]4[N:34]([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[N:33]=[N:32][N:31]=4)[CH2:28][CH2:29]3)[C:3]=12

Participants

Conditions

Temperature: 50 °C

Procedure

To a sealable flask containing ethyl 3-(4-fluoro-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxylate (0.047 g, 0.08 mmol) was added ethanolamine (0.7 mL). The mixture was sealed and heated to 50° C. for 20.5 h. The mixture was cooled to rt, and was diluted with DMF and was passed through a plug of celite to remove any solids. The DMF solution was purified by prep HPLC to give 3-(4-fluoro-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-N-(2-hydroxyethyl)-1-methyl-1H-pyrazole-5-carboxamide.TFA (0.014 g) as an off-white solid. LCMS: m/e 588.7 (M+H)+, ret time 2.03 min (method 2) 1H NMR (500 MHz, CDCl3) δ ppm 8.35 (s, 1H) 8.23 (s, 1H) 7.50-7.61 (m, 6H) 4.29 (s, 3H) 3.78-3.85 (m, 4H) 3.54-3.64 (m, 4H) 3.40 (s, 2H) 3.29-3.34 (m, 2H) 2.79 (s, 1H).

Workup

customThe mixture was sealed
temperatureThe mixture was cooled to rt
customto remove any solids
customThe DMF solution was purified by prep HPLC

Sources & evidence

ORD record: ord-3c587bb3c9554722a669310aa73a809a
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807676B2

Reaction notes

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